Wood isn’t one to let an opportunity slip through his fingers. “I ain’t from the land of dreams,” he told me this past fall. He was raised in Memphis, Tenn., and Birmingham, Ala., and his father was Roy Wood Sr., a radio-journalism pioneer who reported on Black platoons in Vietnam, South African apartheid and the civil rights movement for the Black Chicago radio station WVON before helping found the National Black Network, the first Black-owned radio news service, where he was the news director. His mother, Joyce Dugan, was a respected teacher. Though his parents were highly regarded in the community, Wood’s childhood was sometimes shaped by a sense of scarcity and limitation. “We were raised by people who were fortunate to be able to vote, to drink from the same water fountain,” Wood said. “They were so exhausted from that battle that all they wanted was a house and a fair wage. The idea of dreaming beyond that was not commonplace, and in a lot of instances it was frowned upon. In the South, you dare to dream beyond the horizon.”
His father’s work presented one model for how Wood might dare to dream. When he enrolled at Florida A&M University in 1996, he decided he wanted to work in broadcast journalism, a major that required he take classes in public speaking. He discovered that every time he spoke in front of his classmates, he got laughs without even trying. Wood liked the feeling those laughs gave him, and he started studying the acts of comedians like Adele Givens, Sinbad, Chris Rock and D.L. Hughley. George Carlin, he says, was canon for the fearlessness of his topics and concision with which he expressed opinions that audiences might otherwise find outré. “I used to listen to ‘You Are All Diseased’ once a week, listening to the wordplay and the inflections. It was just perfect. Then I would immediately throw on some Master P.”
In 1998, Wood was arrested after buying clothing with stolen credit cards and was suspended indefinitely from Florida A&M. This youthful indiscretion yielded an unexpected blessing: Wood still received the financial aid he would have used for his tuition, and that money — along with a job as a server at the buffet restaurant Golden Corral in Tallahassee — bankrolled his fledgling comedy career. He took buses across the South, sleeping in bus stations between gigs. When he returned to Birmingham to perform at an open mic at the Stardome, one of his mother’s students saw him and told her about it. She was infuriated and insisted that he focus on getting back in school. Wood eventually did, and even graduated, but he didn’t quit stand-up. Instead he drove out — in a car his mother bought — to cities like Charlotte, sleeping in the passenger seat when he had to. Sometimes, when venues canceled on him, he would take day-labor jobs on construction sites to pay for gas.
Wood’s style was molded by the difficulty of finding his voice in Black clubs across the South. His own middle-class experience of Blackness wasn’t necessarily aligned with his audience’s, and his early jokes — routines about the annoyance of a roommate’s eating your food, for example — didn’t always land. Working those rooms taught him how to craft observational humor in a way that would resonate for everyone from older Black professionals to gang members. But he also learned not to talk down to people. “A Black audience will go with you anywhere on any journey,” he said, “if you make it funny.” He learned to embrace his off-kilter humor without condescending. “That’s what I know about,” he said. “I don’t know about selling weed. That’s not my experience, and my job as a comedian is to present to you my experience. And mine is a weird one.”
